Direct flights from Portland to Chicago
16 nonstop flights a week on 1 airline. Zero layovers — one hop from PDX to MDW.
Flight time: about 3h32m nonstop
Which days does it fly?
When does it fly?
Departure times in Portland local time, from flights observed over the last 7 days.
| Flight | Departs | Duration | Days |
|---|---|---|---|
| Southwest SWA3131 | 1:24a | 3h42m | Fri |
| Southwest SWA799 | 5:37a | 3h32m | Thu |
| Southwest SWA3130 | 6:29a | 3h30m | Mon, Fri |
| Southwest SWA4867 | 7:51a | 3h31m | Sat |
| Southwest SWA2992 | 11:18a | 3h40m | Sun |
| Southwest SWA3130 | 11:22a | 3h26m | Tue–Wed |
| Southwest SWA1351 | 12:00p | 3h26m | Mon, Fri |
| Southwest SWA3131 | 11:32p | 3h32m | Tue, Sat |
| Southwest SWA3131 | 11:38p | 3h34m | Mon, Wed, Fri |
| Southwest SWA3131 | 11:54p | 3h24m | Sun |
Southwest
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The route
One hop: PDX → MDWDrag to pan · scroll with ⌘/Ctrl to zoom · arrow keys when focused
Nonstop from Portland (PDX) to Chicago (MDW)
Portland International Airport (PDX) has 16 nonstop flights a week to Chicago (MDW), operated by Southwest. No layovers, no connections — one hop out of PDX and you're there.
This route flies every day of the week, so any travel day works. Route data updated October 2026 from observed departures.
Route data updated October 2026 from observed flight departures. Schedules change — always confirm with the airline before booking.
How long is the flight from Portland to Chicago?
The nonstop flight from Portland (PDX) to Chicago (MDW) takes about 3h32m in the air, based on recently observed nonstop departures.
How long does it take to drive from Portland to Chicago?
Driving from Portland to Chicago takes about 31h 1m behind the wheel — roughly 2,137 miles, or about 3 days of real driving. The nonstop flight takes about 3h32m.